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Synthesis of a novel tetrahydroisoquinoline pentacyclic framework

, : Synthesis of a novel tetrahydroisoquinoline pentacyclic framework. Tetrahedron 65(11): 2201-2211

N-Acyliminium cyclization of 6-substituted (3R∗,6R∗,11aS∗)-3-arylmethyl-pyrazino[1,2-b]isoquinoline-1,4-diones gave with very good yields a novel tetrahydroisoquinoline pentacyclic core framework (29), while this reaction failed in all-cis-isomers to give instead conjugated enamines by deprotonation. Electronic and steric factors that govern the approach to both diastereomers from 6-substituted pyrazino[1,2-b]isoquinoline-1,4-diones have been studied.


DOI: 10.1016/j.tet.2009.01.051

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